This paper is a methodological contribution to emerging debates on the role of learning, particularly forward-looking (anticipatory) learning, as a key element for adaptation and resilience in the context of climate change. First, we describe two major challenges: understanding adaptation as a process and recognizing the inadequacy of existing learning tools, with a specific focus on high poverty contexts and complex livelihood-vulnerability risks. Then, the article examines learning processes from a dynamic systems perspective, comparing theoretical aspects and conceptual advances in resilience thinking and action research/learning (AR/AL). Particular attention is paid to learning loops (cycles), critical reflection, spaces for learning, and power. Finally, we outline a methodological framework to facilitate iterative learning processes and adaptive decision making in practice. We stress memory, monitoring of key drivers of change, scenario planning, and measuring anticipatory capacity as crucial ingredients. Our aim is to identify opportunities and obstacles for forward-looking learning processes at the intersection of climatic uncertainty and development challenges in Africa, with the overarching objective to enhance adaptation and resilient livelihood pathways, rather than learning by shock.